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Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols

Trifluoromethylated molecules have gained privileged recognition among the medicinal and pharmaceutical chemists. Sustainable photoredox- and electrochemical processes were employed to facilitate the relatively less explored radical cross-electrophile coupling to access trifluoromethyl- and allyl-su...

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Autores principales: Ashraf, Muhammad Awais, Lee, Yunjeong, Iqbal, Naila, Iqbal, Naeem, Cho, Eun Jin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8605352/
https://www.ncbi.nlm.nih.gov/pubmed/34841228
http://dx.doi.org/10.1016/j.isci.2021.103388
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author Ashraf, Muhammad Awais
Lee, Yunjeong
Iqbal, Naila
Iqbal, Naeem
Cho, Eun Jin
author_facet Ashraf, Muhammad Awais
Lee, Yunjeong
Iqbal, Naila
Iqbal, Naeem
Cho, Eun Jin
author_sort Ashraf, Muhammad Awais
collection PubMed
description Trifluoromethylated molecules have gained privileged recognition among the medicinal and pharmaceutical chemists. Sustainable photoredox- and electrochemical processes were employed to facilitate the relatively less explored radical cross-electrophile coupling to access trifluoromethyl- and allyl-substituted tert-alcohols. Reactions proceed through trifluoromethyl ketyl radical and allyl radical intermediates, which undergo challenging radical-radical cross-coupling. The developed transformations are mild and chemo-selective to give cross-coupled products and deliver a wide range of valuable trifluoromethyl- and allyl-containing tertiary alcohols. Both processes can also be applied for the synthesis of amine variant containing trifluoromethyl and allyl moiety, which is considered as amide bioisostere.
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spelling pubmed-86053522021-11-26 Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols Ashraf, Muhammad Awais Lee, Yunjeong Iqbal, Naila Iqbal, Naeem Cho, Eun Jin iScience Article Trifluoromethylated molecules have gained privileged recognition among the medicinal and pharmaceutical chemists. Sustainable photoredox- and electrochemical processes were employed to facilitate the relatively less explored radical cross-electrophile coupling to access trifluoromethyl- and allyl-substituted tert-alcohols. Reactions proceed through trifluoromethyl ketyl radical and allyl radical intermediates, which undergo challenging radical-radical cross-coupling. The developed transformations are mild and chemo-selective to give cross-coupled products and deliver a wide range of valuable trifluoromethyl- and allyl-containing tertiary alcohols. Both processes can also be applied for the synthesis of amine variant containing trifluoromethyl and allyl moiety, which is considered as amide bioisostere. Elsevier 2021-10-30 /pmc/articles/PMC8605352/ /pubmed/34841228 http://dx.doi.org/10.1016/j.isci.2021.103388 Text en © 2021 The Author(s) https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Ashraf, Muhammad Awais
Lee, Yunjeong
Iqbal, Naila
Iqbal, Naeem
Cho, Eun Jin
Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
title Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
title_full Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
title_fullStr Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
title_full_unstemmed Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
title_short Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
title_sort sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8605352/
https://www.ncbi.nlm.nih.gov/pubmed/34841228
http://dx.doi.org/10.1016/j.isci.2021.103388
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